Acetic Acid → 4-Methoxyphenylacetaldehyde

HRID 1729453Notes

Reaction equation

HRID 1729453 reaction equation
C(O)(=O)C.[O:5]1[C:6](=[C:10]1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)C([O-])=O.[K+].C1(C)C=CC=CC=1>O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH:6]=[O:5])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1140TolueneHCID 23705473HCID 23705473, compound

Product 1

HCID 797824-Methoxyphenylacetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

70 ml of an aqueous solution of 3.64 g of acetic acid are added dropwise to a mixture, heated to the boiling point, of 14 g (59 mmol) of potassium (E)-α,β-epoxy-p--methoxycinnamate, 112 ml of toluene and 28 ml of water. After 5 minutes the mixture is cooled to room temperature. The organic phase is washed with water and then with aqueous potassium carbonate solution. The aqueous washings are extracted with toluene. The organic phase is dried azeotropically. The yield of p-methoxyphenylacetaldehyde in the solution obtained amounts to 92-94%.

Workup

  1. washThe organic phase is washed with water
  2. extractionThe aqueous washings are extracted with toluene
  3. customThe organic phase is dried azeotropically

Sources & evidence

ORD record
ord-e9fff2727cab41e8bc77287dc56e9602
Source dataset
uspto-grants-1994_07
Patent number
US05332821

Reaction notes

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